4-[2-(trimethylsilyl)ethynyl]naphthalene-1,8-dicarbonitrile | 1447722-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[2-(trimethylsilyl)ethynyl]naphthalene-1,8-dicarbonitrile
• 英文别名: 4-(2-Trimethylsilylethynyl)naphthalene-1,8-dicarbonitrile；4-(2-trimethylsilylethynyl)naphthalene-1,8-dicarbonitrile
• CAS: 1447722-58-8
• 化学式: C₁₇H₁₄N₂Si
• 分子量: 274.397
• InChiKey: PWNSIFFMLIRRPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[2-(trimethylsilyl)ethynyl]naphthalene-1,8-dicarbonitrile 在 copper(ll) sulfate pentahydrate 、 L-sodium ascorbate 、 盐酸羟胺 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 methyl 2-[4-[(2Z,4Z)-2,4-bis(hydroxyimino)-3-azatricyclo-[7.3.1.0⁵,¹³]trideca-1(12),5,7,9(13),10-pentaen-8-yl]-1H-1,2,3-triazol-1-yl]acetate
  参考文献：
  名称：

  Synthesis of a Hydrophilic Naphthalimidedioxime

  摘要：

  Imidedioximes are formed in hydroxylamine-treated polyacrylonitrile adsorbents used in the extraction of uranium from seawater. Although known to be a good uranophile, the glutarimidedioxime model compound 1 is rapidly hydrolyzed under acidic conditions used to elute metals from the adsorbent. This work reports the synthesis of a hydrophilic naphthalimidedioxime derivative 14, which is stable under acidic elution conditions. The synthesis starts from simple acenaphthenequinone 7 and converts it to a functional group dense imidedioxime 14 in 7 steps.

  DOI：

  10.1021/jo4009386
• 作为产物：
  描述：

  5-溴萘乙基-1,2-二酮 在 copper(l) iodide 、 sulfonamide 、 trans-bis(triphenylphosphine)palladium dichloride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二乙二醇二甲醚 为溶剂， 反应 18.25h， 生成 4-[2-(trimethylsilyl)ethynyl]naphthalene-1,8-dicarbonitrile
  参考文献：
  名称：

  Synthesis of a Hydrophilic Naphthalimidedioxime

  摘要：

  Imidedioximes are formed in hydroxylamine-treated polyacrylonitrile adsorbents used in the extraction of uranium from seawater. Although known to be a good uranophile, the glutarimidedioxime model compound 1 is rapidly hydrolyzed under acidic conditions used to elute metals from the adsorbent. This work reports the synthesis of a hydrophilic naphthalimidedioxime derivative 14, which is stable under acidic elution conditions. The synthesis starts from simple acenaphthenequinone 7 and converts it to a functional group dense imidedioxime 14 in 7 steps.

  DOI：

  10.1021/jo4009386

文献信息

• Synthesis of a Hydrophilic Naphthalimidedioxime
  作者：Christopher D. Grant、Sung Ok Kang、Benjamin P. Hay

  DOI：10.1021/jo4009386

  日期：2013.8.2

  Imidedioximes are formed in hydroxylamine-treated polyacrylonitrile adsorbents used in the extraction of uranium from seawater. Although known to be a good uranophile, the glutarimidedioxime model compound 1 is rapidly hydrolyzed under acidic conditions used to elute metals from the adsorbent. This work reports the synthesis of a hydrophilic naphthalimidedioxime derivative 14, which is stable under acidic elution conditions. The synthesis starts from simple acenaphthenequinone 7 and converts it to a functional group dense imidedioxime 14 in 7 steps.